The present invention relates to a novel class of furan- and thiophenesulfonamide compounds and their use as pre-emergent and post-emergent herbicides and as plant growth regulants.
U.S. Pat. Nos. 4,169,719 and 4,127,405 disclose herbicidal benzene-, furan- and thiophenesulfonamides of general formula ##STR1## where R.sub.1 may be an optionally substituted benzene or a furan or thiophene substituted with H, Cl, Br or CH.sub.3.
U.S. Pat. No. 4,398,939 discloses herbicidal thiophenesulfonamides of formula ##STR2## where R is C.sub.1 -C.sub.4 alkyl, C.sub.3 alkenyl, OCH.sub.3, NO.sub.2, Cl, Br, SO.sub.2 NR.sub.1 R.sub.2 or SO.sub.2 N(OCH.sub.3)CH.sub.3.
European Patent Application (EP-A) No. 30,142, published 6/10/81 discloses herbicidal furan- and thiophenesulfonamides of formula ##STR3## where W' is O or S;
A is C(O)QR.sup.I or C(.dbd.T)R.sup.II ; and PA1 A' is H, Cl, Br, C.sub.1 -C.sub.4 alkyl, OCH.sub.3, NO.sub.2 or CF.sub.3. PA1 R.sub.2 is H, Cl, Br or CH.sub.3 ; PA1 R.sub.2 is H, Cl, Br or CH.sub.3. PA1 R.sub.2 is H, Cl, F, Br, CH.sub.3, OCH.sub.3, CF.sub.3, NO.sub.2, CN or NH.sub.2. PA1 R.sub.2 is H, C.sub.1 -C.sub.3 alkyl, haloalkyl, alkoxy, alkylthio, alkylsulfonyl, halogen, NO.sub.2, CWR.sub.8, SO.sub.2 NR.sub.6 R.sub.7 or COR.sub.9. PA1 Q is halogen, C.sub.1 -C.sub.4 alkyl, cyano, etc.; PA1 R.sub.1 is H, halogen, NO.sub.2 or a group ##STR11## etc.; R.sub.6 is, inter alia, H or C.sub.1 -C.sub.4 alkyl; and R.sub.2 and R.sub.3 can be, among other things, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy. PA1 R.sub.3 is H, C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkoxy; PA1 R.sub.4 and R.sub.5 are independently C.sub.1 -C.sub.2 alkyl; PA1 R.sub.6 and R.sub.7 are independently H or C.sub.1 -C.sub.2 alkyl; PA1 W is O or S; PA1 W.sub.1 is O or S; PA1 Q.sub.1 and Q.sub.2 are independently O, S or NCH.sub.3 ; PA1 A is ##STR15## X is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, halogen, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino or di(C.sub.1 -C.sub.3)alkylamino; PA1 Y is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, halogen, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino, di(C.sub.1 -C.sub.3)alkylamino, C.sub.3 -C.sub.4 alkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, C.sub.2 -C.sub.5 alkylsulfinylalkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.5 alkylsulfonylalkyl, C.sub.3 -C.sub.5 cycloalkyl, C.sub.2 -C.sub.4 alkynyl, C.sub.2 -C.sub.5 alkylthioalkyl, C(O)R.sub.8, ##STR16## N(OCH.sub.3)CH.sub.3 ; m is 2 or 3; PA1 L.sub.1 and L.sub.2 are independently O or S; PA1 R.sub.8 is H or CH.sub.3 ; PA1 R.sub.9 and R.sub.10 are independently C.sub.1 -C.sub.2 alkyl; PA1 R.sub.11 is C.sub.1 -C.sub.3 alkyl; PA1 R.sub.12 is H, F, Cl, NO.sub.2, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkylthio, C.sub.1 -C.sub.2 alkylsulfinyl, C.sub.1 -C.sub.2 alkylsulfonyl, di(C.sub.1 -C.sub.2)alkylsulfamoyl or CO.sub.2 (C.sub.1 -C.sub.2 alkyl); PA1 R.sub.13 is H, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, Cl, F or NO.sub.2 ; PA1 R.sub.14 is H, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 haloalkyl, C.sub.1 -C.sub.3 haloalkoxy, Cl, Br, F, NO.sub.2, di(C.sub.1 -C.sub.3)alkylsulfamoyl, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 alkylsulfinyl, C.sub.1 -C.sub.3 alkylsulfonyl, amino, C.sub.1 -C.sub.3 alkylamino, di(C.sub.1 -C.sub.3)alkylamino, CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3 or CH.sub.2 CN. PA1 Z is CH or N; PA1 Y.sub.1 is O or CH.sub.2 ; PA1 X.sub.1 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or OCF.sub.2 H; and PA1 Y.sub.2 is H or CH.sub.3 ; PA1 X.sub.2 is CH.sub.3, C.sub.2 H.sub.5 or CH.sub.2 CF.sub.3 ; PA1 Y.sub.3 is OCH.sub.3, OC.sub.2 H.sub.5, SCH.sub.3, SC.sub.2 H.sub.5, OCF.sub.2 H, SCF.sub.2 H, CH.sub.3 or C.sub.2 H.sub.5 ; PA1 X.sub.3 is CH.sub.3 or OCH.sub.3 ; PA1 Y.sub.4 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or Cl; and PA1 X.sub.4 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3 or Cl; PA1 (a) when X is Cl, F, Br or I, then Z is CH and Y is OCH.sub.3, OC.sub.2 H.sub.5, N(OCH.sub.3)CH.sub.3, NHCH.sub.3, N(CH.sub.3).sub.2 or OCF.sub.2 H; PA1 (b) when Y is cyclopropyl, X is other than Cl, F, Br or I; PA1 (c) when R.sub.3 is C.sub.1 -C.sub.3 alkoxy, then Q.sub.1 and Q.sub.2 are oxygen; PA1 (d) when R.sub.3 is H or C.sub.1 -C.sub.3 alkyl, then Q is Q-1 through Q-9; PA1 (e) when X or Y is OCF.sub.2 H, then Z is CH; PA1 (f) when the total number of carbon atoms of X and Y is greater than four, then the combined number of carbons of the substituents on Q is less than or equal to ten; PA1 (g) when W is S, then A is A-1, R is H, and Y is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, C.sub.2 H.sub.5, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, OCH.sub.2 CH.sub.2 OCH.sub.3, CH(OCH.sub.3).sub.2 or ##STR17## (h) when A is A-7 and Z is N, then R.sub.3 is C.sub.1 -C.sub.3 alkoxy; (i) when E is CH.sub.2, then R.sub.14 is H, CH.sub.3, OCH.sub.3, Cl or NO.sub.2 and is not in the 4-position. PA1 (1) Compounds of Formula I where R.sub.3 is H or C.sub.1 -C.sub.3 alkyl; PA1 (2) Compounds of Formula I where R.sub.3 is C.sub.1 -C.sub.3 alkoxy; PA1 (3) Compounds of Preferred 1 where PA1 (5) Compounds of Preferred 4 where PA1 (6) Compounds of Preferred 5 where Q.sub.1 and Q.sub.2 are O; PA1 (7) Compounds of Preferred 5 where Q.sub.1 and Q.sub.2 are S; PA1 (8) Compounds of Preferred 5 where Q is Q-1; PA1 (9) Compounds of Preferred 5 where Q is Q-2; PA1 (10) Compounds of Preferred 5 where Q is Q-3; PA1 (11) Compounds of Preferred 5 where Q is Q-4; PA1 (12) Compounds of Preferred 5 where Q is Q-5; PA1 (13) Compounds of Preferred 5 where Q is Q-6; PA1 (14) Compounds of Preferred 5 where Q is Q-7; PA1 (15) Compounds of Preferred 5 where Q is Q-8; PA1 (16) Compounds of Preferred 5 where Q is Q-9; PA1 (17) Compounds of Preferred 2 where PA1 (19) Compounds of Preferred 18 where PA1 (20) Compounds of Preferred 19 where Q is Q-1; PA1 (21) Compounds of Preferred 19 where Q is Q-2; PA1 (22) Compounds of Preferred 19 where Q is Q-3; PA1 (23) Compounds of Preferred 19 where Q is Q-4; PA1 (24) Compounds of Preferred 19 where Q is Q-5; PA1 (25) Compounds of Preferred 19 where Q is Q-6; PA1 (26) Compounds of Preferred 19 where Q is Q-7; PA1 (27) Compounds of Preferred 19 where Q is Q-8; PA1 (28) Compounds of Preferred 19 where Q is Q-9; PA1 (29) Compounds of Preferred 19 where Q is Q-10;
U.S. Pat. No. 4,370,480 teaches herbicidal benzenesulfonamides of general formula ##STR4##
No. EP-A-64,804, published 11/17/82, teaches herbicidal furan- and thiophenesulfonamides of general formula ##STR5## where R.sub.1 is S(O).sub.n R.sub.6 ; and
No. EP-A-13,480 discloses herbicidal pyridinesulfonamides of formula ##STR6## where R.sub.1 is H, Cl, Br, F, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, NO.sub.2 or CO.sub.2 R.sub.5 ; and
No. EP-A-35,893 discloses herbicidal pyridinesulfonamides of formula ##STR7## where R.sub.1 is S(O).sub.n R.sub.3 ; and
No. EP-A-97,122, published Dec. 28, 1983, discloses herbicidal sulfonamides of formula ##STR8## where X is O, S, NR.sub.4 or CR.sub.5 .dbd.N; and
No. EP-A-95,925, published Dec. 7, 1983, and No. EP-A-87,780, published Sept. 7, 1983, teach herbicidal pyrazole sulfonylureas.
No. EP-A-95,925 (published Dec. 7, 1983) and No. EP-A-87,780 (published Sept. 7, 1983) teach herbicidal pyrazole sulfonylureas.
No. EP-A-126,711 (published 11/28/84; Swiss priority 5/16/83) discloses herbicidal sulfonylureas of the formula ##STR9## wherein X is O, S, --NR.sub.5, ##STR10## --CH.dbd.CH-- or an annelated phenyl ring; Z is O or S;